Small update, just FYI and in case anyone ever stumbles upon this problem. Its not a litespeed problem. Its not a mongrel problem. Its a ruby problem. Specifically, its a ruby 1.8.6 problem. rubyonrails.org recommends 1.8.5, however the guide they point to for installation does 1.8.6, and ive seen many OSX port install guides using 1.8.6 (which is what I had done).